CN103012677A - Preparation method of ion imprinted hydroxamic acid chelate resin - Google Patents
Preparation method of ion imprinted hydroxamic acid chelate resin Download PDFInfo
- Publication number
- CN103012677A CN103012677A CN2011102840202A CN201110284020A CN103012677A CN 103012677 A CN103012677 A CN 103012677A CN 2011102840202 A CN2011102840202 A CN 2011102840202A CN 201110284020 A CN201110284020 A CN 201110284020A CN 103012677 A CN103012677 A CN 103012677A
- Authority
- CN
- China
- Prior art keywords
- resin
- metal ion
- acid
- propenyl
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a preparation method of ion imprinted hydroxamic acid chelate resin. According to the invention, propenyl hydroxamic acid is subjected to coordination with imprinting metal ions such as manganese, copper, cobalt, nickel, lanthanum, cerium, yttrium, praseodymium, neodymium, and the like; under the effects of a crosslinking agent and an initiating agent, a propenyl hydroxamic acid-metal ion chelate is polymerized; and the imprinting metal ion is eluted, such that the ion imprinted hydroxamic acid chelate resin is obtained. The method provided by the invention has the advantages of mild reaction condition and high reaction efficiency. The prepared resin has the advantages such as high absorption capacity, high absorption selectivity, and the like.
Description
Technical field
Technical field under the present invention is the preparation of resin, relates generally to the method for a kind of ion blotting hydroximic acid resin of preparation.
Background technology
Hydroximic acid compound is the metal chelator of a quasi-representative, and it exists keto-acid and two kinds of tautomers of pure formula, its keto-acid isomer be otherwise known as hydroxamic acid or hydroxamic acid.Hydroximic acid compound is widely used in flotation, solvent extraction, chemical analysis and the medicine and other fields in the burning ore deposits such as rare earth, titanium, iron because of its unique ligand structure and excellent ligancy, and the hydroximic acid resin also is used to the separation and concentration aspect of the metal ions such as iron, copper, rare earth.
Agrawal etc. are take polystyrene and Acetyl Chloride 98Min. as raw material, have synthesized polychlorostyrene formyl radical vinylbenzene through acetylize, carboxylated and Chloroformylation, have prepared poly-ly to vinylbenzene hydroximic acid resin with azanol reaction again, and resin is to La
3+, Ce
3+, Nd
3+And Y
3+Loading capacity be respectively 0.60,0.62,0.66 and 0.69mmol/g (Y.K.Agrawal, H.Kaur, S.K.Menon.Poly (styrene-p-hydroxamic acids)-synthesis, and ion exchange separation of rare earths.Reactive and Functional Polymers, 1999,39:155-164.).Lee etc. are take ethyl propenoate as monomer, adopt suspension polymerization to prepare the crosslinked divinylbenzene spheroid of polyethyl acrylate, this resin and oxammonium hydrochloride are reacted to make the hydroximic acid resin again under alkaline condition, and resin is to the Cu of 100ppm
2+Has good removal effect (T.S.Lee, D.W.Jeon, J.K.Kim, S.Hong.Formation of metal complex in a poly (hydroxamic acid) resin bead.Fibers and Polymers, 2001,2 (1): 13-17.).Lutfor etc. have prepared polymethacrylate-starch copolymer with methacrylic ester and starch reaction, again multipolymer and oxammonium hydrochloride are reacted in the methanol aqueous solution of alkalescence, made a kind of hydroximic acid resin (M.R.Lutfor, S.Sidik, W.M.Z.Wan Yunus, M.Z.A.Rahman, A.Mansor, M.J.Haron.Synthesis and characterization of poly (hydroxamic acid) chelating resin from poly (methyl acrylate)-grafted sago starch.Journal of Applied Polymer Science, 2001,79 (7): 1256-1264.).
Domestic scholars also has report aspect hydroximic acid resin synthetic.Zhong Hong etc. disclose a kind of method (CN1872885) for preparing the water-soluble polymers that contains hydroxamic acid group of high molecular, this method is dispersed in the water-soluble acrylic polymer powder of high molecular in the polar organic solvent, carry out heterogeneous esterification reaction with alkylating reagent, then carry out heterogeneous hydroxamic acid reaction with hydroxylamine solution, generate the water-soluble polymers that contains hydroxamic acid group of high molecular.Li Haipu to etherification starch and acrylamide and methyl acrylate copolymer carry out respectively the hydroxyl oximation reaction prepared hydroximic acid starch and hydroximic acid polyacrylamide (Li Haipu. the modified high-molecular medicament is to aluminum silicon mineral Action Mechanism of The Flotation and structure one performance study thereof: [doctorate paper]. Changsha: Central South University, 2002).Wang Bi etc. have prepared polyacrylamide under alkaline condition and have contained hydroximic acid side group polymer chelating agent (king is green with azanol reaction, Xu Guili, Hu Xingqi. contain the research that lead waste water is processed in the agent of hydroximic acid side group high molecular heavy metals trapping. chemical research and application, 2008,20 (5): 561～564).Zhu Changying etc. take triallyl isocyanuric acid ester and Vinylstyrene mixing Crosslinked Macroporous polyacrylonitrile resin as parent and azanol under alkaline condition, react, synthesized amidoxime-hydroxyl oxime hybrid resin (Zhu Changying, Qian Tingbao, high battle-axe used in ancient China. the oximation reaction of triallyl isocyanuric acid ester and Vinylstyrene mixing Crosslinked Macroporous polyacrylonitrile resin. ion-exchange and absorption, 1989,5 (2): 81～86).
Research trends both domestic and external be the analysis showed that, the synthetic of hydroximic acid resin is to adopt to carry out the hydroximic acid modification with polymers such as polystyrene, polyacrylic ester, polyacrylamide, polyacrylonitrile, starch mostly at present, be subjected to the impact of high molecular weight reactive efficient, prepared resin functional group content is low, skewness is restricted the absorption property of resin.
Summary of the invention
The purpose of this invention is to provide a kind of method for preparing ion blotting hydroximic acid resin, the hydroximic acid resin loading capacity that makes by the present invention is larger, adsorption selectivity is higher.
Technical scheme of the present invention is:
Propenyl hydroximic acid and the metallic print ion that will have formula I structural formula are carried out coordination reaction, obtain propenyl hydroximic acid-chelate of metal ion;
R in the formula
1Be hydrogen atom, methyl, ethyl, phenyl or cyano group, R
2Be hydrogen atom, methyl, phenyl or tolyl;
Described metallic print ion is a kind of in the divalent-metal ion of manganese, copper, cobalt, nickel, or a kind of in the trivalent metal ion of lanthanum, cerium, yttrium, praseodymium, neodymium;
Make propenyl hydroximic acid-chelate of metal ion under the effect of initiator, dispersion agent, linking agent and pore-creating agent, carry out polyreaction, make solid resin; The consumption of initiator, dispersion agent, linking agent, pore-creating agent is respectively 2%～10%, 3%～10%, 1%～15%, 1%～10% of propenyl hydroximic acid quality;
The resin that polyreaction obtains is put into elutriant, and mechanical stirring or vibration are with the metal ion on the wash-out resin; Or resin put into adsorption column elutriant drip washing, with the metal ion wash-out; Elutriant comprises in hydrochloric acid, nitric acid, the dilute sulphuric acid one or more; The resin that obtains behind the wash-out is ion blotting hydroximic acid resin.
Behind the divalent-metal ion or the trivalent metal ion coordination of lanthanum, cerium, yttrium, praseodymium, neodymium etc. of the present invention by propenyl hydroximic acid and manganese, copper, cobalt, nickel etc., under the effect of linking agent, make the polymerization of propenyl hydroximic acid, and then with the coordination of metal ion wash-out, obtain ion blotting hydroximic acid resin.Structural unit shown in the described ion blotting hydroximic acid resin molecular structural formula IV.
R in the formula
1Be hydrogen atom, methyl, ethyl, phenyl or cyano group, R
2Be hydrogen atom, methyl, phenyl or tolyl.
The compound (such as methyl acrylate or methyl methacrylate) that the present invention will have structure shown in the formula II reacts under the condition of the existence of sodium hydroxide (potassium) with the hydroxylamine compound with structure shown in the formula III, makes the propenyl hydroximic acid.The mol ratio of the hydroxylamine compound of structure shown in the compound of structure, the formula III, sodium hydroxide (potassium) is 1: 1～1.6: 1～2.5 shown in its Chinese style II, preferred 1: 1.1～1.3: 1.8～2.2; Temperature of reaction is 30～90 ℃, preferred 60～70 ℃; Reaction times is 2～10h, preferred 3～5h.
R in the formula
1Be hydrogen atom, methyl, ethyl, phenyl or cyano group, R
2Be hydrogen atom, methyl, phenyl or tolyl.
Make propenyl hydroximic acid and metallic print ion coordination, obtain propenyl hydroximic acid-chelate of metal ion.Under metallic print ion comprise the trivalent metal ion of the divalent-metal ion of manganese, copper, cobalt, nickel etc. or lanthanum, cerium, yttrium, praseodymium, neodymium etc.The mol ratio of propenyl hydroximic acid and metal ion is n: 0.1～1, and preferred n:0.4～0.6, wherein n is the metal ion valence state; The concentration of metal ion solution is 0.01～1mol/L, preferred 0.1～0.2mol/L; Temperature of reaction is 20～90 ℃, preferred 30～40 ℃; Reaction times is 1～3h, preferred 1～2h.Reaction process needs according to the concentration of metal ion and precipitation pH value regulator solution acidity thereof, and the general control pH is 3～5.
Make propenyl hydroximic acid-chelate of metal ion under the effect of initiator, dispersion agent, linking agent, pore-creating agent, carry out polymerization, make solid resin.Described initiator comprises dibenzoyl peroxide or azo dibutyronitrile etc.; described dispersion agent comprises gelatin, polyvinyl alcohol, calcium carbonate, calcium sulfate, magnesiumcarbonate or sal epsom etc.; described linking agent comprises methacrylate second diester (EGDMA), divinylbenzene (DVB) or N; the diene based compounds such as N-methylene-bisacrylamide (MBA), described pore-creating agent comprises No. 200 gasoline, benzene or toluene etc.The consumption of initiator is 2%～10%, preferred 3%～5% of propenyl hydroximic acid quality; Dispersant dosage is 3%～10%, preferred 4%～5%; Dosage of crosslinking agent is 1%～15%, preferred 6%～10%; The pore-creating agent consumption is 1%～10%, preferred 2%～4%; Temperature of reaction is 20～90 ℃, preferred 50～60 ℃; Reaction times is 2～5h, preferred 3～4h.For polyreaction is carried out fully, can on the basis of above-mentioned reaction, under 80～120 ℃ temperature, continue reaction 1～3h.
The resin that polyreaction obtains is put into elutriant, and mechanical stirring or vibration are with the metal ion on the wash-out resin; Or resin put into adsorption column drip washing, with the metal ion wash-out.Described eluent comprises hydrochloric acid, nitric acid, dilute sulphuric acid or its mixture, also can add a kind of in thiocarbamide, methyl alcohol or the ethanol in above-mentioned acid.The mass percent concentration of acid is 5%～20%, preferred 10%～15%; The mass percent concentration of thiocarbamide is 0%～10%, preferred 5%～8%; The mass percent concentration of methyl alcohol or ethanol is 0%～30%, preferred 10%～20%.When mechanical stirring or vibration wash-out, eluting temperature is 20～90 ℃, preferred 30～40 ℃; Elution time is 2～5h, preferred 3～4h.During wash-out, eluting temperature is 10～90 ℃, generally at room temperature carries out in adsorption column; Eluent flow rate is 0.5～20ml/min, preferred 1～5ml/min; The elutriant consumption is 1～20 bed volume, preferred 2～5 bed volume.
The resin that obtains behind the wash-out is ion blotting hydroximic acid resin of the present invention.But the resin hygrometric state is preserved, and also can save backup after the drying.
Description of drawings
Fig. 1 is the infrared spectrogram of resin 1 with the resin 2 of embodiment 1 preparation.
Fig. 2 is the resin 2 and resin 3 Adsorption of Cu of embodiment 1 preparation
2+Adsorption isothermal curve.
Fig. 3 is the resin 4 absorption La of embodiment 2 preparations
3+, Ce
3+And Y
3+The isothermal adsorption curve.
Embodiment
The present invention is further specified by the following example, but is not subjected to the restriction of these embodiment.
Synthetic and the absorption property of embodiment 1 cupric ion trace hydroximic acid resin
It is that 1: 1 solution dissolves that 0.12mol oxammonium hydrochloride and 0.20mol sodium hydroxide are put into 100ml methyl alcohol and water volume ratio, again the 0.1mol methyl acrylate is slowly added solution, and the control temperature of reaction is 60 ℃ of reaction 5h, obtains propenyl hydroximic acid solution.Be about 4 with sulfuric acid regulation solution pH value, add 100ml0.20mol/L pH value and be 4 copper-bath, at 30 ℃ of lower 2h that react.The benzoyl peroxide of 0.5g polyvinyl alcohol, 0.5g divinylbenzene and 0.5g is added in the solution, at 60 ℃ of lower reaction 3h, obtain resin 1.Filter, after the washing, resin is put into band plug Erlenmeyer flask, add again 50mL 1mol/L sulfuric acid, at 40 ℃ of lower vibration 4h, filter, at 60 ℃ of dry 1h, obtain cupric ion trace hydroximic acid resin (resin 2).Resin 1 is seen Fig. 1 with the infrared spectrogram of resin 2.
According to the preparation process condition of resin 2, omit two steps of trace ion on trace ion and the coordination of propenyl hydroximic acid and the wash-out resin, prepare common hydroximic acid resin (resin 3), be used for comparing the absorption property of resin 2 and resin 3.
Get 0.1g resin 2 or resin 3 and 25ml Cu
2+Starting point concentration is 0.5～3.0mgml
-1, pH is 2.5 solution, adds in the tool plug Erlenmeyer flask of 100ml, put into again in the water bath with thermostatic control vibrator, 25 ℃ of control adsorption temps, adsorption time is 3h.Adsorb complete after, measure Cu in the solution
2+Concentration, calculate the loading capacity of resin.Resin 2 and resin 3 Adsorption of Cu
2+Adsorption isothermal curve see Fig. 2.
Synthetic and the absorption property of embodiment 2 rare earth ion trace hydroximic acid resins
The synthetic method of propenyl hydroximic acid is identical with embodiment 1.Be about 5 with nitric acid regulator solution pH value, add 100ml 0.20mol/L pH value and be 5 lanthanum nitrate, cerous nitrate or yttrium nitrate solution, at 30 ℃ of lower 1h that react.The benzoyl peroxide of 0.5g polyvinyl alcohol, 0.01g Sodium dodecylbenzene sulfonate, 0.5g divinylbenzene, 0.5g vinylbenzene and 0.5g is added in the solution, at 60 ℃ of lower reaction 3h, obtain resin.Filter, after the washing, resin is put into band plug Erlenmeyer flask, add again 50mL 1mol/L sulfuric acid, at 40 ℃ of lower vibration 4h, obtain rare earth ion trace hydroximic acid resin.The resin of preparation is designated as respectively resin 4, resin 5 and resin 6 take lanthanum, cerium, yttrium as the trace ion.
Get 0.25g resin 4 and 25ml La
3+, Ce
3+Or Y
3+Starting point concentration is 0.5～2.5mgml
-1, pH is 5 solution, adds in the tool plug Erlenmeyer flask of 100ml, put into again in the water bath with thermostatic control vibrator, 25 ℃ of control adsorption temps, adsorption time is 6h.Adsorb complete after, measure La in the solution
3+, Ce
3+Or Y
3+Concentration, calculate the loading capacity of resin.Resin 4 absorption La
3+, Ce
3+And Y
3+The isothermal adsorption curve see Fig. 3.
Claims (12)
1. the preparation method of an ion blotting hydroximic acid resin, propenyl hydroximic acid and the metallic print ion that will have formula I structural formula are carried out coordination reaction, obtain propenyl hydroximic acid-chelate of metal ion;
R in the formula
1Be hydrogen atom, methyl, ethyl, phenyl or cyano group, R
2Be hydrogen atom, methyl, phenyl or tolyl;
Described metallic print ion is a kind of in the divalent-metal ion of manganese, copper, cobalt, nickel, or a kind of in the trivalent metal ion of lanthanum, cerium, yttrium, praseodymium, neodymium;
Make propenyl hydroximic acid-chelate of metal ion under the effect of initiator, dispersion agent, linking agent and pore-creating agent, carry out polyreaction, make solid resin;
The resin that polyreaction obtains is put into elutriant, and mechanical stirring or vibration are with the metal ion on the wash-out resin; Or resin put into adsorption column elutriant drip washing, with the metal ion wash-out; Elutriant comprises in hydrochloric acid, nitric acid, the dilute sulphuric acid one or more; The resin that obtains behind the wash-out is ion blotting hydroximic acid resin.
2. method according to claim 1, the mol ratio of propenyl hydroximic acid and metal ion is that n: 0.1～1, n is the metal ion valence state; The concentration of metal ion solution is 0.01～1mol/L; The coordination reaction temperature is 20～90 ℃, and the reaction times is 1～3h, and reaction process control pH is 3～5.
3. method according to claim 2, the mol ratio of propenyl hydroximic acid and metal ion is n: 0.4～0.6, the concentration 0.1～0.2mol/L of metal ion solution, the coordination reaction temperature is 30～40 ℃, the reaction times is 1～2h.
4. method according to claim 1, described initiator comprises dibenzoyl peroxide or azo dibutyronitrile, described dispersion agent comprises gelatin, polyvinyl alcohol, calcium carbonate, calcium sulfate, magnesiumcarbonate or sal epsom, described linking agent comprises methacrylate second diester, divinylbenzene or N,N methylene bis acrylamide; Described pore-creating agent comprises gasoline, benzene or toluene No. 200.
5. method according to claim 4, the consumption of initiator, dispersion agent, linking agent, pore-creating agent is respectively 2%～10%, 3%～10%, 1%～15%, 1%～10% of propenyl hydroximic acid quality, polymeric reaction temperature is 20～90 ℃, and the reaction times is 2～5h.
6. method according to claim 5, the consumption of initiator, dispersion agent, linking agent, pore-creating agent is respectively 3%～5%, 4%～5%, 6%～10%, 2%～4% of propenyl hydroximic acid quality, polymeric reaction temperature is 50～60 ℃, and the reaction times is 3～4h.
7. described method is carried out fully for making polyreaction according to claim 4-6, on the basis of described polyreaction, continues reaction 1～3h under 80～120 ℃ temperature.
8. method according to claim 1 is added thiocarbamide, methyl alcohol or ethanol in the acid of elutriant; The mass percent concentration of the acid of elutriant is 5%～20%; The mass percent concentration of thiocarbamide is 0%～10%, and the mass percent concentration of methyl alcohol or ethanol is 0%～30%; When mechanical stirring or vibration wash-out, eluting temperature is 20～90 ℃, and elution time is 2～5h; During wash-out, eluting temperature is 10～90 ℃ in adsorption column, and eluent flow rate is 0.5～20ml/min, and the elutriant consumption is 1～20 bed volume.
9. method according to claim 8, the mass percent concentration of the acid of elutriant is 10%～15%; The mass percent concentration of thiocarbamide is 5%～8%, and the mass percent concentration of methyl alcohol or ethanol is 10%～20%; Mechanical stirring or vibration eluting temperature are 30～40 ℃, and elution time is 3～4h; Eluting temperature is room temperature in the adsorption column, and eluent flow rate is 1～5ml/min, and the elutriant consumption is 2～5 bed volume.
10. method according to claim 1, described propenyl hydroximic acid with formula I structural formula be by the compound with structure shown in the formula II with have the reaction of the hydroxylamine compound of structure shown in the formula III and obtain;
R in the formula
1Be hydrogen atom, methyl, ethyl, phenyl or cyano group, R
2Be hydrogen atom, methyl, phenyl or tolyl.
11. method according to claim 10, the compound with structure shown in the formula II reacts under the condition of the existence of sodium hydroxide or potassium hydroxide with the hydroxylamine compound with structure shown in the formula III, makes the propenyl hydroximic acid; The mol ratio of the hydroxylamine compound of structure and sodium hydroxide or potassium hydroxide shown in the compound of structure shown in the formula II, the formula III is 1: 1～1.6: 1～2.5; Temperature of reaction is 30～90 ℃; Reaction times is 2～10h.
12. method according to claim 11, the mol ratio of the hydroxylamine compound of structure and sodium hydroxide or potassium hydroxide shown in the compound of structure shown in the formula II, the formula III is 1: 1.1～1.3: 1.8～2.2; Temperature of reaction is 60～70 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110284020.2A CN103012677B (en) | 2011-09-23 | 2011-09-23 | Preparation method of ion imprinted hydroxamic acid chelate resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110284020.2A CN103012677B (en) | 2011-09-23 | 2011-09-23 | Preparation method of ion imprinted hydroxamic acid chelate resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103012677A true CN103012677A (en) | 2013-04-03 |
| CN103012677B CN103012677B (en) | 2015-03-04 |
Family
ID=47961821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110284020.2A Active CN103012677B (en) | 2011-09-23 | 2011-09-23 | Preparation method of ion imprinted hydroxamic acid chelate resin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103012677B (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103521197A (en) * | 2013-10-15 | 2014-01-22 | 杭州电子科技大学 | Preparation method of light rare earth ion imprinted adsorbent for treating rare earth wastewater |
| CN103804571A (en) * | 2013-08-26 | 2014-05-21 | 中国科学院城市环境研究所 | Nuclear shell temperature and PH double hypersensitivity metallic ion printing nanometer gel and preparation method thereof |
| CN104877059A (en) * | 2015-05-08 | 2015-09-02 | 中南大学 | Crosslinked polystyrene-polypropenyl hydroximic acid inter-penetrating network resin and preparation method and application thereof |
| CN105087931A (en) * | 2015-09-15 | 2015-11-25 | 成都理工大学 | Method for purifying rare earth mother liquor by means of printed materials |
| CN107629178A (en) * | 2017-09-18 | 2018-01-26 | 湖南大学 | Hydroximic acid type montmorillonite ion blotting material and its preparation method and application |
| CN108144591A (en) * | 2018-02-10 | 2018-06-12 | 安徽唯诗杨信息科技有限公司 | A kind of epoxy resin adsorbent and its application based on molecular engram |
| CN109926028A (en) * | 2019-04-24 | 2019-06-25 | 陕西科技大学 | A kind of thiocarbamide trace resin and preparation method thereof and the application in ADSORPTION OF GOLD |
| CN110325597A (en) * | 2017-03-17 | 2019-10-11 | 住友精化株式会社 | Water absorbency resin composition, absorber and absorbent commodity |
| WO2020041991A1 (en) * | 2018-08-29 | 2020-03-05 | 中南大学 | Hydroximic acid-metal hydroxide coordination complex, and preparation and application thereof |
| RU2782753C2 (en) * | 2018-08-29 | 2022-11-02 | Сентрал Сауф Юниверсити | Complex compound of hydroxamic acid and metal hydroxide, its preparation and use |
| CN115463644A (en) * | 2021-06-11 | 2022-12-13 | 中国石油化工股份有限公司 | Polyacrylonitrile mercury ion adsorption resin and preparation method and application thereof |
| CN115819652A (en) * | 2022-12-06 | 2023-03-21 | 中南大学 | 2-amino pentanedioxyhydroxamic acid modified polyacrylic acid chelating resin and preparation method and application thereof |
| CN115819909A (en) * | 2022-10-27 | 2023-03-21 | 广东省科学院资源利用与稀土开发研究所 | Macroporous acrylic hydroximic acid chelating resin and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5983730A (en) * | 1982-11-05 | 1984-05-15 | Agency Of Ind Science & Technol | Recovery of minute amount of metal ion |
| CN1872885A (en) * | 2005-06-03 | 2006-12-06 | 中南大学 | Method for preparing water-soluble polymer of containing hydroxamic acid group in high molecular weight |
-
2011
- 2011-09-23 CN CN201110284020.2A patent/CN103012677B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5983730A (en) * | 1982-11-05 | 1984-05-15 | Agency Of Ind Science & Technol | Recovery of minute amount of metal ion |
| CN1872885A (en) * | 2005-06-03 | 2006-12-06 | 中南大学 | Method for preparing water-soluble polymer of containing hydroxamic acid group in high molecular weight |
Non-Patent Citations (4)
| Title |
|---|
| GEORGE M ISKANDER ET AL: ""Synthesis and copolymerization of methacryloyl hydroxamic acids"", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
| 张骞: ""羟肟酸树脂的合成及其对矿山酸性废水的吸附特性研究"", 《中国优秀硕士学位论文全文数据库•工程科技I辑》 * |
| 张骞: ""羟肟酸树脂的合成及其对矿山酸性废水的吸附特性研究"", 《中国优秀硕士学位论文全文数据库•工程科技I辑》, no. 3, 15 March 2011 (2011-03-15) * |
| 范洪涛等: ""离子印记聚合物及其在分析化学中的应用"", 《化学通报》 * |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804571A (en) * | 2013-08-26 | 2014-05-21 | 中国科学院城市环境研究所 | Nuclear shell temperature and PH double hypersensitivity metallic ion printing nanometer gel and preparation method thereof |
| CN103804571B (en) * | 2013-08-26 | 2016-08-31 | 中国科学院城市环境研究所 | A kind of hud typed temperature and pH Lazer property metal ion trace nanogel and preparation method thereof |
| CN103521197A (en) * | 2013-10-15 | 2014-01-22 | 杭州电子科技大学 | Preparation method of light rare earth ion imprinted adsorbent for treating rare earth wastewater |
| CN103521197B (en) * | 2013-10-15 | 2015-04-29 | 杭州电子科技大学 | Preparation method of light rare earth ion imprinted adsorbent for treating rare earth wastewater |
| CN104877059A (en) * | 2015-05-08 | 2015-09-02 | 中南大学 | Crosslinked polystyrene-polypropenyl hydroximic acid inter-penetrating network resin and preparation method and application thereof |
| CN105087931A (en) * | 2015-09-15 | 2015-11-25 | 成都理工大学 | Method for purifying rare earth mother liquor by means of printed materials |
| CN105087931B (en) * | 2015-09-15 | 2017-06-30 | 成都理工大学 | A kind of method that use imprinted material carries out edulcoration purification to rare earth mother solution |
| CN110325597A (en) * | 2017-03-17 | 2019-10-11 | 住友精化株式会社 | Water absorbency resin composition, absorber and absorbent commodity |
| CN107629178A (en) * | 2017-09-18 | 2018-01-26 | 湖南大学 | Hydroximic acid type montmorillonite ion blotting material and its preparation method and application |
| CN108144591B (en) * | 2018-02-10 | 2020-12-01 | 灵璧县浩翔信息科技有限公司 | Epoxy resin adsorbent based on molecular imprinting and application thereof |
| CN108144591A (en) * | 2018-02-10 | 2018-06-12 | 安徽唯诗杨信息科技有限公司 | A kind of epoxy resin adsorbent and its application based on molecular engram |
| RU2782753C2 (en) * | 2018-08-29 | 2022-11-02 | Сентрал Сауф Юниверсити | Complex compound of hydroxamic acid and metal hydroxide, its preparation and use |
| WO2020041991A1 (en) * | 2018-08-29 | 2020-03-05 | 中南大学 | Hydroximic acid-metal hydroxide coordination complex, and preparation and application thereof |
| CN109926028B (en) * | 2019-04-24 | 2022-01-28 | 陕西科技大学 | Thiourea imprinted resin, preparation method thereof and application thereof in gold adsorption |
| CN109926028A (en) * | 2019-04-24 | 2019-06-25 | 陕西科技大学 | A kind of thiocarbamide trace resin and preparation method thereof and the application in ADSORPTION OF GOLD |
| CN115463644A (en) * | 2021-06-11 | 2022-12-13 | 中国石油化工股份有限公司 | Polyacrylonitrile mercury ion adsorption resin and preparation method and application thereof |
| CN115463644B (en) * | 2021-06-11 | 2023-12-08 | 中国石油化工股份有限公司 | Polyacrylonitrile mercury ion adsorption resin and preparation method and application thereof |
| CN115819909A (en) * | 2022-10-27 | 2023-03-21 | 广东省科学院资源利用与稀土开发研究所 | Macroporous acrylic hydroximic acid chelating resin and preparation method thereof |
| CN115819909B (en) * | 2022-10-27 | 2024-05-03 | 广东省科学院资源利用与稀土开发研究所 | Macroporous acrylic hydroxamic acid chelate resin and preparation method thereof |
| CN115819652A (en) * | 2022-12-06 | 2023-03-21 | 中南大学 | 2-amino pentanedioxyhydroxamic acid modified polyacrylic acid chelating resin and preparation method and application thereof |
| CN115819652B (en) * | 2022-12-06 | 2023-09-05 | 中南大学 | 2-aminopentanedioxime acid modified polyacrylic acid chelate resin and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103012677B (en) | 2015-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103012677B (en) | Preparation method of ion imprinted hydroxamic acid chelate resin | |
| Zong et al. | Synthesis of polyacrylonitrile-grafted cross-linked N-chlorosulfonamidated polystyrene via surface-initiated ARGET ATRP, and use of the resin in mercury removal after modification | |
| CN103159888B (en) | Primary amine groups resin of a kind of acrylic acid series Large Copacity trapping cupric ion and preparation method thereof | |
| Lou et al. | Acrylic acid-functionalized metal–organic frameworks for Sc (III) selective adsorption | |
| CN102580701B (en) | Preparation method of arsenic removal resin | |
| Nishihama et al. | Separation of lanthanum and cerium using a coated solvent-impregnated resin | |
| CN106334537A (en) | Magnetic mesoporous silica surface-imprinted polymer adsorbing material and preparation method thereof | |
| Abd El-Magied et al. | Studies on the recovery of Th (IV) ions from nitric acid solutions using amino-magnetic glycidyl methacrylate resins and application to granite leach liquors | |
| Long et al. | Binding mechanism of the amidoxime functional group on chelating resins toward gallium (III) in Bayer liquor | |
| CN106699952B (en) | A kind of preparation method of the magnetic imprinted polymer of phenyl boric acid fundamental mode | |
| CN104774283A (en) | Acrylic acid pyridine chelating resin as well as preparation method and application thereof | |
| CN103193928B (en) | Coordination imprinted polymer and preparation method thereof | |
| CN103450394B (en) | A kind of preparation method of cupric ion imprinted polymer adsorbent | |
| KR20090074208A (en) | An ion exchange resin and a process for the use thereof | |
| CN104356298A (en) | Solid phase imprinted double-position extraction agent for copper (II) and preparation method of extraction agent | |
| CN115784509A (en) | TOC removing process in cobalt chloride production process | |
| JP2023543516A (en) | New chelate resin | |
| JP6758283B2 (en) | Sulfonated and aminomethylated chelate resin | |
| CN106582569A (en) | Ion imprinted impregnating resin and preparation method thereof | |
| CN108250372B (en) | Hydrophilic magnetic styrene strong base anion exchange microsphere resin and preparation method thereof | |
| Zhang et al. | Synthesis of Cu (II) ion-imprinted polymers as solid phase adsorbents for deep removal of copper from concentrated zinc sulfate solution | |
| CN101402033A (en) | Chelate adsorption material and method of producing the same | |
| CN104877059A (en) | Crosslinked polystyrene-polypropenyl hydroximic acid inter-penetrating network resin and preparation method and application thereof | |
| Hainey et al. | Oligoamine-functionalised poly (glycidyl methacrylate-ethyleneglycol dimethacrylate) resins as moderate base extractants for gold from cyanide solutions | |
| CN107573462B (en) | Copper (II) ion surface imprinted polymer and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |